4350-44-1Relevant academic research and scientific papers
Michael addition of ethyl acetoacetate to α,β-unsaturated oximes in the presence of FeCl3: A novel synthetic route to substituted nicotinic acid derivatives
Chibiryaev,De Kimpe,Tkachev
, p. 8011 - 8013 (2000)
The FeCl3-catalyzed reaction of α,β-unsaturated oximes with ethyl acetoacetate resulted in Michael addition followed by ring closure to produce substituted nicotinic acid derivatives in a very efficient way. (C) 2000 Elsevier Science Ltd.
Rhenium-catalyzed regioselective synthesis of multisubstituted pyridines from β-enamino ketones and alkynes via C-C bond cleavage
Yamamoto, Shun-Ichi,Okamoto, Kana,Murakoso, Makiko,Kuninobu, Yoichiro,Takai, Kazuhiko
supporting information; experimental part, p. 3182 - 3185 (2012/07/28)
A new method is described for the regioselective synthesis of multisubstituted pyridine derivatives. Treatment of N-acetyl β-enamino ketones with alkynes in the presence of the rhenium catalyst, Re 2(CO)10, gives multisubstituted pyridines regioselectively. In this reaction, the N-acetyl moieties are important for the selective formation of the multisubstituted pyridines. This reaction proceeds via insertion of alkynes into a carbon-carbon single bond of β-enamino ketones, intramolecular nucleophilic cyclization, and elimination of acetic acid.
Non-peptide NK1 receptor ligands based on the 4-phenylpyridine moiety
Giuliani, Germano,Cappelli, Andrea,Matarrese, Mario,Masiello, Valeria,Turolla, Elia Anna,Monterisi, Cristina,Fazio, Ferruccio,Anzini, Maurizio,Pericot Mohr, Gal.La,Riitano, Daniela,Finetti, Federica,Morbidelli, Lucia,Ziche, Marina,Giorgi, Gianluca,Vomero, Salvatore
experimental part, p. 2242 - 2251 (2011/05/06)
The quinoline nucleus of the previously described 4-phenylquinoline-3- carboxamides NK1 receptor ligands 7 has been transformed into either substituted or azole - (i.e., triazole or tetrazole) fused pyridine moieties of compounds 9 and 10, resp
Cerium catalysed Michael addition to α,β-unsaturated oximes: A facile and efficient synthesis of substituted pyridines
Kumar, Sanjay,Saini, Anil,Sandhu, Jagir S.
, p. 429 - 432 (2007/10/03)
CeCl3.7H2O-Nal is found to be an effective catalyst for the synthesis of various tetra-substituted pyridine derivatives via Michael addition of β-dicarbonyl compounds to α,β-unsaturated oximes and subsequent ring closure by cyclo-deh
One-pot multistep Bohlmann-Rahtz heteroannulation reactions: Synthesis of dimethyl sulfomycinamate
Bagley, Mark C.,Chapaneri, Krishna,Dale, James W.,Xiong, Xin,Bower, Justin
, p. 1389 - 1399 (2007/10/03)
(Chemical Equation Presented) The synthesis of dimethyl sulfomycinamate, the acidic methanolysis product of the sulfomycin family of thiopeptide antibiotics, from methyl 2-oxo-4-(trimethylsilyl)but-3-ynoate is achieved in a 2,3,6-trisubstituted pyridine synthesis that proceeds with total regiocontrol in 13 steps by the Bohlmann-Rahtz heteroannulation of a 1-(oxazol-4-yl)enamine or in 12 steps and 9% yield by three-component cyclocondensation with N-[3-oxo-3-(oxazol-4-yl)propanoyl]serine and ammonia in ethanol.
Ionic liquid promoted simple and efficient synthesis of β-enamino esters and β-enaminones from 1,3-dicarbonyl compounds - One-pot, three-component reaction for the synthesis of substituted pyridines
Karthikeyan, Ganesan,Perumal, Paramasivan T.
, p. 1746 - 1751 (2007/10/03)
A facile enamination of 1,3-dicarbonyl compounds with amines has been developed that affords good to excellent yields of β-enamino esters and β-enaminones using Bronsted acidic ionic liquid 1-methylimidazolium trifluoroacetate ([Hmim]+Tfa-) at room temperature. This methodology has been extended for the synthesis of substituted pyridines in excellent yield by a one-pot, three-component reaction of 1,3-dicarbonyl compounds, ammonium acetate, and alkynone in the presence of [Hmim] +Tfa-.
New N-halosuccinimide-mediated reactions for the synthesis of pyridines
Bagley, Mark C.,Glover, Christian,Merritt, Eleanor A.,Xiong, Xin
, p. 811 - 814 (2007/10/03)
5-Bromo-2,6-dialkylpyridine-4-carboxylates are generated in excellent yield by the Michael addition of enaminoesters and ethynyl ketones followed by bromocyclization using N-bromosuccinimide within 1 hour at 0°C. Treatment of the same aminopentadienone intermediates with N-iodosuccinimide facilitates a low temperature cyclodehydration under very mild conditions to give 2,3,6-trisubstituted pyridines with total regiocontrol.
A new mild method for the one-pot synthesis of pyridines
Xiong, Xin,Bagley, Mark C.,Chapaneri, Krishna
, p. 6121 - 6124 (2007/10/03)
Polysubstituted pyridines are prepared in good yield and with total regiocontrol by the one-pot reaction of an alkynone, 1,3-dicarbonyl compound and ammonium acetate in alcoholic solvents. This new three-component heteroannulation reaction proceeds under mild conditions in the absence of an additional acid catalyst and has been used in the synthesis of dimethyl sulfomycinamate, the acidic methanolysis degradation product of the sulfomycin family of thiopeptide antibiotics.
A novel indium-catalysed synthesis of tetra-substituted pyridine derivatives
Saikia, Promod,Prajapati, Dipak,Sandhu, Jagir S.
, p. 8725 - 8727 (2007/10/03)
Indium trichloride was found to be an effective catalyst for the synthesis of various tetra-substituted pyridine derivatives via Michael addition of β-dicarbonyl compounds to α,β-unsaturated oximes and subsequent ring closure.
A new one-step synthesis of pyridines under microwave-assisted conditions
Bagley, Mark C,Lunn, Rebecca,Xiong, Xin
, p. 8331 - 8334 (2007/10/03)
Tri- or tetrasubstituted pyridines are prepared by microwave irradiation of ethyl β-aminocrotonate and various alkynones in a single synthetic step and with total control of regiochemistry. This new one-pot Bohlmann-Rahtz procedure conducted at 170°C in a
